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GIMP Brush for drawing Buildings

I wanted to be able to put down drawings in a quick but realistic fashion.

To this end, I created a animated brush. This brush will "paint" buildings along a path. I set it up to follow the curve with 18 degree image rotations, and it randomly chooses one of four building shapes.

Attached are:

- a sample showing how it strokes along a path (dashed red line)

- sample map using this technique. I made the roads quickly using paths, stoked them with a wide brush in the road color. I then selected the road. enlarged the selection by 10 px, then converted the selection to a new path then stroked that with the paintbrush, using the building brush. A few pretty-ups (buildings were embossed and given drop shadow) and the road was given a gradient overlay to give the illusion of wear (and stroked)

I used virtually this same technique to make the small buildings for this map. It's a great way to lay them down quickly, but I think I went back and hand edited a few of them just to give some extra variety.
This was done in Adobe Illustrator.

I'm guessing that the fill technique that Keith mentioned is what would be used to fill in an area with buildings as well? This is a good technique for a more 'modern' town, but early medieval and most fantasy wouldn't be as structured, or am I wrong about that?

I thought that exact same thing the first time I saw this type of town drawing, but in fact the lining of the road method appears to have been typical in the medieval towns of England, at least. Look at John Speed's set of early 1600s maps for examples:

From Speed's depictions we can see that "road lining" was true of even large towns/small cities such as York, but not of large cities such as London wherein buildings are crowded together into true city blocks.

I thought that exact same thing the first time I saw this type of town drawing, but in fact the lining of the road method appears to have been typical in the medieval towns of England, at least. Look at John Speed's set of early 1600s maps for examples:

From Speed's depictions we can see that "road lining" was true of even large towns/small cities such as York, but not of large cities such as London wherein buildings are crowded together into true city blocks.

Yeah, this is very common. The inner areas were frequently used for plating, livestock, storage, gardens, what-have-you. I just finished a map of 17th Century New Amsterdam (New York), which was a prime example of this pattern.
If anything, the "blocks" of buildings I did on my Tharad map are more unrealistic, being the sort of structure you would only find in much larger and more established cities, once with much more of an outlying support structure.